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Personne :
Carreras, Virginie

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Carreras

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Virginie

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Université Laval. Département de chimie

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ncf11909919

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  • PublicationAccès libre
    Asymmetric Cu1-Catalyzed Insertion Reaction of 1-Aryl-2,2,2- trifluoro-1-diazoethanes into Si–H Bonds
    (American Chemical Society, 2019-10-28) Ollevier, Thierry; Carreras, Virginie; Gandon, Vincent; Besnard, Claire
    An asymmetric copper(I)-catalyzed Si−H insertion reaction of 1-aryl-2,2,2-trifluoro-1-diazoethanes in dimethyl carbonate as a green solvent alternative was developed. A C2-symmetric copper(I) diimine complex enabled the asymmetric insertion reaction to give enantioenriched (1-aryl-2,2,2-trifluoroethyl)silanes with excellent stereoselectivities (up to 98:2 er). Successful conversion of the silanes into the corresponding alcohols was performed with retention of stereochemistry. Mechanistic studies and DFT calculations support the proposed model for the observed stereoselectivities.
  • PublicationAccès libre
    Asymmetric Diels–Alder reaction of α,β-unsaturated oxazolidin-2-one derivatives catalyzed by a chiral Fe(III)-bipyridine diol complex
    (ACS Publications, 2018-02-08) Ollevier, Thierry; Carreras, Virginie; Jalba, Angela; Li, Mao
    An asymmetric FeIII-bipyridine diol catalyzed Diels–Alder reaction of α,β-unsaturated oxazolidin-2-ones has been developed. Among various FeII/FeIII salts, Fe(ClO4)3·6H2O was selected as the Lewis acid of choice. The use of a low catalyst loading (2 mol % of Fe(ClO4)3·6H2O and 2.4 mol % of Bolm’s ligand) afforded high yields (up to 99%) and high enantiomeric excesses (up to 98%) of endo-cycloadducts for the Diels–Alder reaction between cyclopentadiene and substituted acryloyloxazolidin-2-ones. Other noncyclic dienes led to decreased enantioselectivities. A proposed model supports the observed stereoinduction.